Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects
文献类型：期刊论文
| 作者 | Zhang XH(张夏衡)1; ZHOU YU1; Zuo JP(左建平)1; Yu B(俞飚)1 |
| 刊名 | Nat. Commun.
 |
| 出版日期 | 2015 |
| 卷号 | 6页码:5879 |
| 其他题名 | 具有免疫抑制活性的杠柳孕甾苷Periploside A的全合成 |
| 通讯作者 | 俞飚 |
| 英文摘要 | Periploside A is a pregnane hexasaccharide identified from the Chinese medicinal plant Periploca sepium, which features a unique seven-membered formyl acetal bridged orthoester (FABO) motif and potent immunosuppressive activities. Here, we show the synthesis of this molecule in a total of 76 steps with the longest linear sequence of 29 steps and 9.2% overall yield. The FABO motif is constructed via a combination of Sinay's and Crich's protocol for the formation of orthoester and acetal glycosides, respectively. The 2-deoxy-beta-glycosidic linkages are assembled stereoselectively with judicious choice of the glycosylation methods. The epimer at the spiro-quaternary carbon in the FABO motif has also been elaborated in a stereo-controlled manner. This epimer, as well as the synthetic analogues bearing the FABO motif, retain largely the inhibitory activities of periploside A against the proliferation of T-lymphocyte, indicating the importance of the chemical connection of the FABO motif to their immunosuppressive activity. |
| 学科主题 | 生命有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1038/ncomms6879 |
| 语种 | 英语 |
| WOS记录号 | WOS:000348702400003 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39481]  |
| 专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
| 作者单位 | 1.中科院上海有机化学研究所, 生命有机化学国家重点实验室 2.中科院上海药物研究所 |
| 推荐引用方式 GB/T 7714 | Zhang XH,ZHOU YU,Zuo JP,et al. Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects[J]. Nat. Commun.,2015,6:5879. |
| APA | 张夏衡,ZHOU YU,左建平,&俞飚.(2015).Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects.Nat. Commun.,6,5879. |
| MLA | 张夏衡,et al."Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects".Nat. Commun. 6(2015):5879. |
入库方式： OAI收割
来源：上海有机化学研究所
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